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Retirement: A Piece of Cake.

I’d never met him before. I wouldn’t even know him if we bumped straight into each other on the street. Hell, I don’t even know his real name… but Gary (we’ll call him from here on out) has taken up residence in my brain for well over a decade now.

But this story about Gary, actually starts LONG before Gary, this story actually starts with my dad, because without knowing my dad’s UPS stories, I probably couldn’t appreciate Gary’s, quite the same way.

My dad was a 40 year career “UPS-Man,” and while I wasn’t around for all those years, I was around for a lot of them.

I have memories of company picnics, Softball tournaments, Bring Your Kid To Work Day (when Dad was still working in the old parts building, long before his branch would close and he’d start the back breaking job of delivering packages), and everything that came after.

My dad though has different memories. And his memories, and his subsequent stories, are better. A lot better.

The stories he could tell… so many stories… bad, good, and everything in between and well Gary, Gary falls in between… somewhere just at the tail end of my dad’s 40 year stint working for ‘Brown.’

Now again to preface this story, because we don’t want “Gary” sounding like a complete asshole, because I’d like to think he wasn’t, one would HAVE to know something about UPS… delivery drivers specifically… and what one would absolutely have to know about those UPS employees is that those ladies and gentlemen may get paid bank… BUT… they bust their asses for every single, jolly, copper red cent they earned and then some. THIS I learned from my dad’s 40 year UPS career….

“Big, BIG, Energy”

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Now I get it, any full time job is “tough” and all workers deserve to be paid a living wage for a full, hard day of work, and with this I would agree… but THESE folks are WORKING HARD, HARD.

How hard?

Well I’d tell you a lot more stories about the absolute chaos that is the loading and unloading of packages from feeders and overnight air, the trucks stuffed so full they could’t even sneak an extra envelope in, and all the men and women busting ass to get you your stuff. But I won’t, you’ll just have to believe me when I say: these people work really damn hard.

And unlike some other high paying and rewarding jobs, delivering packages for UPS was something you did for the paycheck, the killer benefits, the stock options, and not because you “loved what you were doing.” Delivering packages was just that… it was just what you were doing, hoping to God you made it till retirement day without keeling over, so you could cash in and punch out for good… no more being harassed by your supervisor over mere seconds on a delivery… over holding keys correctly… over exiting the truck properly.

And what exactly could one expect after spending a lifetime busting ass to the grindstone for Big Brown?

Like clockwork, the last two days of all UPS drivers’ careers ended the same way: a full day of paperwork with HR on day one and a little “party” in the break room on day two, the final day of one’s UPS career.

If you’re wondering, because you probably are (and this is integral to the story), the big retirement party would consist of a grocery store sheet-cake with “Congratulations on your retirement, __________” and the person’s name scrawled across the cake’s bottom. You’d get a handshake from your supervisor (who most likely rode your ass over “those 6 seconds you wasted THIS delivery” every other shift up until then), along with the ‘privilege’ of being allowed to sit in the break room for the day, saying your “good-byes” to the other UPS-ers hurriedly leaving from and going to work.

That was it. 40 years and you got a handshake and a sheet cake and a day in the break room.

On a side note, and a testament to just how crappy of a job package delivery was/is, my dad was convinced that the only reason you were even taken off the road those last two days, had way more to do with UPS not wanting their employees to be tempted to put a brick on the gas pedal of the delivery truck and drive that bitch through a guardrail and off a bridge and less to do with UPS’s generosity and their true appreciation of one slaving the last 40 years of one’s life in pursuit of the perfect package shipment, but I digress….

Which again, brings us to “Gary,” that guy my dad used to work with….

Now my dad wasn’t even there on Gary’s last day. No… he only heard the story from several of his coworkers when he got back from vacation; they all had their own versions, slightly different but with the same delicious twist at the end…

As was customary, Gary had spent his second to last, uneventful day with HR filling out paperwork. I’d like to imagine that there were a couple forced “corporate” laughs as he filled out all his forms, the same old tired, lame HR jokes, and Gary, just sitting there, going through the motions. I’d like to think that Gary wasn’t premeditating at this point… Gary was just processing.

And what a thing to process! An entire career. 40 years of one’s life. Gone. Over. Maybe the best years? Maybe not. But either way, an era was over.

I picture HR smiling at this point, shaking his hand as Gary snaps out of his daydream, they make another not so funny joke about “the end of an era, ey’ Gary?” as they extend their hands to shake. Gary grunts as he shakes their hands… expressionless. He walks out the door, letting it shut loudly behind him with a finality he’s beginning to appreciate. “The end of an era indeed,” he grunts to himself.

On Gary’s last day his coworkers were gathered, as was customary in the break room. Most of them there just as much, if not more so, for the sheet cake than for Gary and his actual retirement party. My dad’s friends would later tell him that everyone had already gotten their small styrofoam plates and plastic forks in preparation of the cake being cut when Gary “just appeared”. A few people were talking quietly amongst themselves, Gary’s supervisor was craning his head, looking over the small groups of brown hatted-heads to see if Gary had made his way in yet. And then he was there.

Now I know that Gary walked in through the doors, just like any other flesh and blood human being in that there break room, but legends…. Legends like Gary, they just appear. And that’s exactly how everyone who was there remembered it and would tell the story from there on out: Gary just showed up out of nowhere and walked over to the cake and his supervisor, who smiled, “There he is, the man of the hour,” with his hand extended for his obligatory shake.

Except Gary wasn’t having it. He waved him off and a hush fell over the break room.

I think Gary had snapped, though I don’t think snap would be the right word for what happened next; when he saw his shitty supervisor, standing in front of his shitty grocery store sheet cake, as a big “thank you” for giving the majority of his life for a back breaking and soul crushing job, Gary decided in that moment, that he was done with the facade, the stupid charades, the fake HR smiles, the lame pc jokes, the fucking handshakes…

And Gary just did what he did… on impulse… no… no… it wasn’t about impulse, he did what he did on principle:

Gary walked over to the cake but didn’t say a word. He looked at it, expressionless, he looked it over and quietly he picked it up. Everyone was watching him but it happened so fast; he confidently walked his cake clear across the break room, his monochromatic coworkers looking on, styrofoam plates and flaccid plastic forks in hand, and he just launched that fucking sheet cake into the god damn trash pail. Everyone’s jaws dropped.

“The REAL party is at the bar down the street. If you want to say good bye, I’ll see you there.”

And just like that Gary left. He was gone. Leaving an absolutely stunned group of people in his wake and a mediocre, albeit perfectly good grocery store sheet cake in the trash: which is exactly how Gary became both a retiree and UPS break room legend.


My dad retired a few years after “that guy that he used to work with.” So of course when my dad retired, I had to ask him, knowing damn well he never would, if he had tossed his cake in the trash can too? My dad laughed and told me “No,” then added, “But they did spell my name wrong on the cake… 40 years and they spelled my name wrong,” my dad laughed.

I asked my dad if anyone had taken Gary up on his party, if anyone had met him at the bar after the little cake fiasco. I had never thought to ask that before…

“Oh yeah,” he said chuckling, “a couple of the guys met him over there after work. They all laughed about the cake… they had a great time.”


In my mind I like to picture Gary at the bar. His few but real friends from work have long since left, as have most of the other patrons. It’s dark and cold outside, almost time to close up. In front of Gary are two empty pint glasses, he stands up and pulls his wallet out of his company issued UPS brown slacks, he takes out a fifty dollar bill, folds it in half vertically and places it on the bar by his empty glasses and an old ring of condensation.

He looks over Frank’s Bar one last time, he knows he’s never coming back, his new life starts tomorrow. He’s almost halfway to the door when the bartender notices the $50 and calls out, “Hey mister, you need some change?” But Gary waves him off without turning and then… the bartender calls out again, just as Gary reaches the door and the cold winter night waiting for him on the other side, “You forgot your coat,” he says, reaching over the counter to pick up the thick brown coat hung over the back of the bar stool.

“I won’t need that anymore. Keep it… or (he now smiles) toss it in the trash,” Gary says as he walks out, jacket-less, into the cold dark night.

And then Gary’s walking, and he’s smiling, the first real smile he’s smiled in a long damn time.

The bartender picks up the jacket, carefully examining the thick and well made coat. He notices the UPS insignia, and what appears to be a single fleck of bright blue frosting on the chest…


I also like to think that Gary decided to live his life unfiltered that very moment he pitched the cake. And while I think the pitching of the cake is badass af (and something I would totally never do, lol) I think the gesture was in and of itself where all the meaning was: bucking unquestioned custom, throwing your own version of a real retirement party for yourself, taking matters into one’s own hands, writing your own destiny, creating your own path, and staying true to yourself, sappy HR handshake or not…

In that beautiful, awe inspiring, cake pitching moment, Gary wasn’t living his life for the comfort of others, no - Gary was living life in the moment, unfiltered, and on his own terms.

Now, I’m not telling you to go pitch your three year old nephew’s birthday cake into the trash as a bevy of horrified onlookers hold their empty plates, as you unintelligibly ramble on about how “this party is lame and the real one is at the bar”… I can assure you, it won’t get the same effect, but what I am saying though, is that there’s a time for eating cake, and a time for tossing it (and your cares about what anyone else thinks of you) right in the trash as you boldly move on with your life… exactly how you envision that AND doing it 100% on your own terms.

And for this, I’d love to thank “Gary” wherever he may be, for the all the inspiration.

“F*ck. This. Sh*t.”

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